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A Jail Visit with the Alleged Dread Pirate Roberts

Lauren Smiley | Photo: Facebook | October 18, 2013

The accused drug kingpin Ross Ulbricht grants his first interview.

Past the metal detector, the buzz-in security door, and the inmates chatting with Sunday visitors at an Alameda County jail, the man accused of being the Dread Pirate Roberts, the alleged mastermind of the world’s biggest online drug bazaar known as Silk Road, stands behind a plexiglas window in a claustrophobic booth.

Inmate ULW981—real name Ross William Ulbricht—is 29 years old, 6-foot-2, 145 pounds, and ready to grant his first jail interview after being arrested on federal drug trafficking, computer hacking, and money laundering charges. Freshly shaven, Ulbricht wears a red Alameda County Jail XL jumpsuit, his wrists shackled to his waist. His auburn brown hair is combed into a wave above his elfin features, his gaze intense, his skin looking in need of some sun. He sits his beanpole frame on the other side of the window, hands on his hips, bony elbows nearly touching the two beige walls.

He says that I am the first reporter he’s spoken to. He’s been advised by his government-provided attorney not to talk with the press. But he can’t help himself; he wanted “to see what it would be like” to be interrogated by a member of the media. He’s also, apparently, lonely. Though he was just visited by his self-identified best friend René Pinnell, he’s still in the mood for more company—any company. I suggest that talking to me must be better than staring at a prison cell wall. He wryly agrees.

He playfully raises a foot up over the table—no shoe, just a sock and a flip flop—to show me that he is free of the ankle shackles he’d worn in federal court in San Francisco last Wednesday. Shuffling into the courtroom that morning, Ulbricht, through his attorney, had denied that he was the Dread Pirate Roberts, and agreed to be extradited to New York City to face charges.

Before his arrest two weeks ago, Ulbricht tells me that he led “a pretty private life” in San Francisco, where he moved to last fall. There were few people in the city who really knew him, he says. Even fewer who might have guessed at the double life he was allegedly leading. Before FBI agents descended on a community library in the sleepy Glen Park neighborhood to arrest Ulbricht two weeks ago, he had kept a decidedly low profile. Even his friend Pinnell told the press that the Feds must have gotten the wrong guy. Ulbricht’s former roomates on 15th Avenue told a Forbes reporter they only knew him as Joshua Terrey, a reclusive freelance currency trader who was always on his computer.

But underneath that quiet exterior, federal prosecuters claim, was a combustible cocktail of hubris, cyber savvy, and a fierce desire to protect his fortune. The feds accuse Ulbricht of facilitating $1.2 billion in drug deals over Silk Road’s two and a half year existence—all transacted in the online currency of Bitcoin. (The FBI has been unable to decrypt Ulbricht’s personal Bitcoin cache—another $80 million, an FBI spokesperson told Forbes—because they can’t get the passsword from Ulbricht.). Ulbricht was also indicted in Maryland federal court this month just days after the Silk Road charges came down: He’s been accused of ordering a $80,000 murder-for-hire hit on a former Silk Road employee who Ulbricht allegedly believed had been stealing users’ money.

The Ulbricht I meet is every bit the same calm, circumspect, and intensely introverted man who appears in a YouTube video taped last December in San Francisco for StoryCorps StoryBooth, an oral history project that airs on NPR and local radio stations. (On the video, Pinnell identifies Ulbricht as a “currency trader” and Ulbricht quietly waxes, in his laconic Texas drawl, about his early sexual and drug experiences and states, without irony, that, in 20 years, he wants to have had a “substantial positive impact on the future of humanity.”)

Now, Ulbricht awaits extradition from the Glenn Dyer Jail in downtown Oakland. “I think they want me,” he says, meaning that he expects the transfer to New York to come soon, though he doesn’t know the date. Though I’m carrying no pen, paper, or recording device—the jail won’t allow them—Ulbricht is extremely cautious with his answers. He says that from his “side of the glass,” he has to be careful. He’s facing a life sentence in prison and doesn’t know the prosecution’s full case against him. He doesn’t want to say anything to me that will be held against him. Our conversation has several stops and starts as he clams up to any question about his case—does he want to comment on his guilt or innocence? “No.” Will he be posting bail? ‘No comment.” Who’s been visiting him in jail? What internet cafes did he work out of in San Francisco? Nothing, nothing. At one point he even says we should talk about me. The only subject about which he will truly open up is his jail life.

“This is the first time I’ve been arrested,” Ulbricht volunteers. Really, I ask, no DUIs, no college high jinks? “Nope.” He tells me very matter of factly that he spends 20 to 22 hours a day in his cell alone, with just a window in the door to the pod, and a blurred one to the outdoors. He gets let out for showers or to go out to the yard accompanied by guards, but not with other inmates. He can hear other prisoners talking through the walls, but rarely adds anything. His daily interactions: a few comments with guards, one hour of phone time a day to family members and friends who’ve registered to receive his calls. He eats in his cell—the food’s not half bad, he says. The other inmates in his pod know who he is from watching the TV news, but Ulbricht has no view of the TV from his cell.

Of course—do I need to even ask?—he isn’t permitted internet access. For a man who allegedly built the world’s most intricately connected online drug empire, Ulbricht now finds himself in the most unlikely of places: Totally out of the loop. He says he’s been “isolated” from the wall-to-wall press coverage that’s been dissecting everything about his life, from his high school pencil drawings to his adult turn towards libertarianism. I tell him about the reporter from Forbes who tracked down his former roommates on 15th Avenue, and he looks astonished. He repeats the statement back to me as a question, unbelieving. When I say his name on Google brings up an endless string of news stories about his takedown, he replies that it used to only bring up hits about his accomplishments in physics.

I ask him if he is scared about the future. “Not excessively,” he says. (He seems to have chosen that phrase carefully. When I later quote him back as saying “not necessarily,” he snaps, “That’s not what I said.”) Perhaps some of his seeming zen about the future can be explained by a Facebook manifesto he penned back in 2010: "Is it possible for someone locked in a cage to be freer than someone who isn’t? What if they are free from limiting beliefs and can imagine experiences without limits, while the other limits themselves to a prison of dull routines?" When I ask him if he’s bored in custody, he shakes his head no.

He says that he had wanted to have people talk on his behalf to the press, but that everyone who knows him has now been advised to stay quiet. Eventually, he’ll have important things to say, but for now he has to keep mum—characterizing the whole experience of getting interviewed when he’s not supposed to be giving up information as “not very pleasant.”

After 15 minutes, time is up and Ulbricht heads back to his largely solitary jailbird existence: writing and reading letters from family and friends (he says no admirers have written him yet), making “doodles,” and reading the novel his parents sent him—“Master and Commander” by Patrick O’Brian. It’s the first of a 20-book series about a British naval captain’s adventures on the high seas. Facing life in prison, and steep odds against being offered bail, Ulbricht may have time to get through them all.